Ethanol → Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405186

반응식

HRID 405186 반응식
[CH:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([C:13]([F:16])([F:15])[F:14])=[CH:5][C:4]=1[C:17]1[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=1)=O.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1.CCO.[BH4-].[Na+]>CS(C)=O.C(Cl)Cl.O>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[CH:45]=[CH:44][C:43]([NH:46][CH2:1][C:3]3[C:8]([C:9]([F:12])([F:10])[F:11])=[CH:7][C:6]([C:13]([F:14])([F:15])[F:16])=[CH:5][C:4]=3[C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=3)=[CH:42][CH:41]=2)=[CH:38][CH:39]=1

참가 물질

8

반응물 4

HCID 702Ethanol2회HCID 86754-Amino-4'-chlorodiphenylHCID 4311764Sodium borohydride2회HCID 86674260Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

생성물 1

HCID 86674261Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate (76 mg, 0.16 mmol) and 4′-chloro-[1,1′-biphenyl]-4-amine (40 mg, 0.20 mmol) in DMSO (0.16 mL) was stirred at 100° C. After 30 min EtOH (0.16 mL) was added and the resulting homogeneous solution was stirred at 100° C. After 1 h the resulting homogeneous solution was cooled to room temperature, and NaBH4 (20 mg, 0.53 mmol), EtOH (1 mL), and DMSO (0.5 mL) were added and the resulting mixture was stirred. After 30 min, additional NaBH4 (20 mg, 0.53 mmol) was added and the resulting homogeneous solution was stirred. After 20 min the resulting mixture was diluted with DCM (5 mL) and 1 M NaH2PO4 (4 mL) was carefully added. Water was added and the aqueous phase was extracted with DCM. The combined organic layers were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

후처리

  1. temperatureAfter 1 h the resulting homogeneous solution was cooled to room temperature
  2. stirringthe resulting mixture was stirred
  3. stirringthe resulting homogeneous solution was stirred
  4. additionwas carefully added
  5. extractionthe aqueous phase was extracted with DCM
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-cf1fef51d5b3431c96f6ea6a8cd4ae49
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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